Rh(II)-Catalyzed C–N Bond Formation Using Enynones and N–H Imines: An Approach to Diarylmethylamines

A Rh(II)-catalyzed furyl carbene
N–H insertion reaction
involving an N-sp2-hybridized imine is
described, which represents an atom-economical route by which to access
diarylmethylamine derivatives with high efficiency and broad substrate
scope. An unusual reaction mechanism is proposed, in which the rhodium
catalyst plays a dual role in facilitating enynone cyclization via
activation and enhancement of the nucleophilicity of the NH imine.